CA1321606C - Procede pour la fabrication de lubrifiant synthetique a partir d'oligmeres d'olefine - Google Patents

Procede pour la fabrication de lubrifiant synthetique a partir d'oligmeres d'olefine

Info

Publication number: CA1321606C
Authority: CA; Canada
Prior art keywords: olefin; trimer; alpha; promoter; synlube
Prior art date: 1988-06-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA000601711A

Other languages

English (en)

Inventor

Matthew J. Lynch

Marshall B. Nelson

Thomas J. Dileo

Ronny Wen-Long Lin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BP Corp North America Inc

Original Assignee

Ethyl Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-06-27

Filing date

1989-06-05

Publication date

1993-08-24

1989-06-05 Application filed by Ethyl Corp filed Critical Ethyl Corp

1993-08-24 Application granted granted Critical

1993-08-24 Publication of CA1321606C publication Critical patent/CA1321606C/fr

2010-08-24 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 26
150000001336 alkenes Chemical class 0.000 title abstract description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract description 3
239000013638 trimer Substances 0.000 claims abstract description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 22
239000000178 monomer Substances 0.000 claims description 18
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 16
239000000539 dimer Substances 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 3
125000003158 alcohol group Chemical group 0.000 claims 1
230000003197 catalytic effect Effects 0.000 claims 1
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
-1 methyl butyate Chemical class 0.000 description 4
239000000047 product Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
230000003606 oligomerizing effect Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
238000006384 oligomerization reaction Methods 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
229940093475 2-ethoxyethanol Drugs 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
- C10G50/02—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation of hydrocarbon oils for lubricating purposes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1213—Boron fluoride
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Inorganic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Lubricants (AREA)

CA000601711A 1988-06-27 1989-06-05 Procede pour la fabrication de lubrifiant synthetique a partir d'oligmeres d'olefine Expired - Fee Related CA1321606C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US212,020		1980-12-01
US21202088A	1988-06-27	1988-06-27

Publications (1)

Publication Number	Publication Date
CA1321606C true CA1321606C (fr)	1993-08-24

Family

ID=22789232

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000601711A Expired - Fee Related CA1321606C (fr)	1988-06-27	1989-06-05	Procede pour la fabrication de lubrifiant synthetique a partir d'oligmeres d'olefine

Country Status (3)

Country	Link
EP (1)	EP0349276B1 (fr)
CA (1)	CA1321606C (fr)
DE (1)	DE68921799T2 (fr)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0764757B2 (ja) *	1990-09-20	1995-07-12	出光石油化学株式会社	オレフィンオリゴマーの製造方法
WO2000026261A1 (fr) *	1998-10-29	2000-05-11	Nippon Petrochemicals Company, Limited	Methode d'extraction et de recuperation de trifluorure de bore a l'aide de fluorure de metal et procede de production de polyolefines utilisant cette methode
US7989670B2 (en)	2005-07-19	2011-08-02	Exxonmobil Chemical Patents Inc.	Process to produce high viscosity fluids
WO2007011462A1 (fr)	2005-07-19	2007-01-25	Exxonmobil Chemical Patents Inc.	Lubrifiants obtenus à partir de charges d'alpha-oléfines mélangées
US8748361B2 (en)	2005-07-19	2014-06-10	Exxonmobil Chemical Patents Inc.	Polyalpha-olefin compositions and processes to produce the same
US8501675B2 (en)	2006-06-06	2013-08-06	Exxonmobil Research And Engineering Company	High viscosity novel base stock lubricant viscosity blends
US8921290B2 (en)	2006-06-06	2014-12-30	Exxonmobil Research And Engineering Company	Gear oil compositions
US8834705B2 (en)	2006-06-06	2014-09-16	Exxonmobil Research And Engineering Company	Gear oil compositions
US8299007B2 (en)	2006-06-06	2012-10-30	Exxonmobil Research And Engineering Company	Base stock lubricant blends
US8535514B2 (en)	2006-06-06	2013-09-17	Exxonmobil Research And Engineering Company	High viscosity metallocene catalyst PAO novel base stock lubricant blends
JP5555490B2 (ja)	2006-07-19	2014-07-23	エクソンモービル・ケミカル・パテンツ・インク	メタロセン触媒を用いたポリオレフィンの製造方法
US8513478B2 (en)	2007-08-01	2013-08-20	Exxonmobil Chemical Patents Inc.	Process to produce polyalphaolefins
US9469704B2 (en)	2008-01-31	2016-10-18	Exxonmobil Chemical Patents Inc.	Utilization of linear alpha olefins in the production of metallocene catalyzed poly-alpha olefins
US8865959B2 (en)	2008-03-18	2014-10-21	Exxonmobil Chemical Patents Inc.	Process for synthetic lubricant production
EP2283050B1 (fr)	2008-03-31	2012-05-09	ExxonMobil Chemical Patents Inc.	Fabrication d'une pao haute viscosité stable au cisaillement
US8394746B2 (en)	2008-08-22	2013-03-12	Exxonmobil Research And Engineering Company	Low sulfur and low metal additive formulations for high performance industrial oils
US8247358B2 (en)	2008-10-03	2012-08-21	Exxonmobil Research And Engineering Company	HVI-PAO bi-modal lubricant compositions
US8716201B2 (en)	2009-10-02	2014-05-06	Exxonmobil Research And Engineering Company	Alkylated naphtylene base stock lubricant formulations
CA2782873C (fr)	2009-12-24	2016-06-28	Exxonmobil Chemical Patents Inc.	Procede de production d'huiles de base synthetiques inedites
US8728999B2 (en)	2010-02-01	2014-05-20	Exxonmobil Research And Engineering Company	Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient
US8748362B2 (en)	2010-02-01	2014-06-10	Exxonmobile Research And Engineering Company	Method for improving the fuel efficiency of engine oil compositions for large low and medium speed gas engines by reducing the traction coefficient
US8642523B2 (en)	2010-02-01	2014-02-04	Exxonmobil Research And Engineering Company	Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient
US8598103B2 (en)	2010-02-01	2013-12-03	Exxonmobil Research And Engineering Company	Method for improving the fuel efficiency of engine oil compositions for large low, medium and high speed engines by reducing the traction coefficient
US8759267B2 (en)	2010-02-01	2014-06-24	Exxonmobil Research And Engineering Company	Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient
US9815915B2 (en)	2010-09-03	2017-11-14	Exxonmobil Chemical Patents Inc.	Production of liquid polyolefins
WO2013055481A1 (fr)	2011-10-10	2013-04-18	Exxonmobil Research And Engineering Company	Compositions d'huile pour moteurs à haute efficacité

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4045508A (en) *	1975-11-20	1977-08-30	Gulf Research & Development Company	Method of making alpha-olefin oligomers
US4045507A (en) *	1975-11-20	1977-08-30	Gulf Research & Development Company	Method of oligomerizing 1-olefins
EP0079335A4 (fr) *	1981-05-22	1983-09-02	Gulf Research Development Co	Oligomerisation d'alpha-olefines avec un catalyseur heterogene.

1989
- 1989-06-05 CA CA000601711A patent/CA1321606C/fr not_active Expired - Fee Related
- 1989-06-27 EP EP19890306527 patent/EP0349276B1/fr not_active Expired - Lifetime
- 1989-06-27 DE DE1989621799 patent/DE68921799T2/de not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0349276A3 (en)	1990-05-16
DE68921799D1 (de)	1995-04-27
EP0349276A2 (fr)	1990-01-03
EP0349276B1 (fr)	1995-03-22
DE68921799T2 (de)	1995-07-13

Legal Events

Date	Code	Title	Description
2003-08-25	MKLA	Lapsed

Publication	Publication Date	Title
CA1321606C (fr)	1993-08-24	Procede pour la fabrication de lubrifiant synthetique a partir d'oligmeres d'olefine
CA1320220C (fr)	1993-07-13	Procede pour l'obtention d'un lubrifiant de synthese a base d'oligomere olefinique
US4910355A (en)	1990-03-20	Olefin oligomer functional fluid using internal olefins
EP0377306B1 (fr)	1992-08-19	Procédé de préparation de cooligomères hydrogénés
US3760026A (en)	1973-09-18	Synthesis of di-tert-butylethylene using olefin disproportionation
US4434309A (en)	1984-02-28	Oligomerization of predominantly low molecular weight olefins over boron trifluoride in the presence of a protonic promoter
EP0077113B1 (fr)	1986-09-03	Oligomérisation d'oléfines à l'utilisation de trifluorure de bore et un catalyseur contenant trois composantes
CA1325229C (fr)	1993-12-14	Procede pour la production de lubrifiants synthetiques de type oligomeres d'olefine
CA1324618C (fr)	1993-11-23	Procede synlute
US4417082A (en)	1983-11-22	Thermal treatment of olefin oligomers via a boron trifluoride process to increase their molecular weight
US5120891A (en)	1992-06-09	Process for oligomerizing olefins using a super-dealuminated Y-zeolite
US5191139A (en)	1993-03-02	Process for oligomerizing olefins using sulfate-activated group IV oxides
US5146030A (en)	1992-09-08	Process for oligomerizing olefins using halogen-free titanium salts or halogen-free zirconium salts on clays
GB2123434A (en)	1984-02-01	Oligomerization of olefins
US5191130A (en)	1993-03-02	Process for oligomerizing olefins using halogenated phosphorous-containing acid on montmorillonite clay
US4906798A (en)	1990-03-06	High viscosity index olefin oligomer process
US5243118A (en)	1993-09-07	Process for oligomerizing olefins using sulfate-activated molecular sieves
EP0549156A1 (fr)	1993-06-30	Procédé pour l'oligomérisation d'oléfines utilisant des sels de titane ou de zirconium déposé sur de dioxyde de silice
EP0515022A2 (fr)	1992-11-25	Procédé pour la fabrication d'oligomères
CA2046374A1 (fr)	1992-01-31	Procede d'oligomerisation d'olefines au moyen d'heteropolyacides sur supports inertes
CA2085433A1 (fr)	1993-06-24	Methode pour l'oligomerisation d'olefines a l'aide de sels de titane ou de zirconium deposes sur du dioxyde de silicium
EP0785245A2 (fr)	1997-07-23	Procédé d'oligomérisation d'oléfines